Jenna , Stephen Ch. 01


(Author’s Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!)


Jenna and I have been friends for nearly 15 years. We dated ever so briefly about 12 years ago, but nothing more than kissing and heavy petting occurred before she decided it wasn’t going to work out. At the time I was heart-broken, but looking back now, I realize she was correct that we weren’t right for one another. Our friendship remained alive however, and it was probably stronger now than ever before.

We now shared a bond that neither of us had ever wanted: as divorced parents. My marriage went off the rails a little over a year ago, hers about five months ago. Since her wedded “bliss” came to a screeching halt, she and I had grown even closer, as I have been there to support her and walk her through the early stages of life as a divorcee.

On a muggy Saturday afternoon in June, we were at her place by her backyard pool, enjoying a drink or two… which soon became six or seven. This had us a bit loopy and lacking our normal inhibitions. As a result, our discussion became far more probing and flirty than our usual normal chit chat.

“Okay, I have a question,” she declared. “What is the kinkiest thing you’ve ever done,” she asked me.

I laughed a nervous laugh. “I’ve done a few things, but if I told you then I’d have to kill you.”

She pushed further, but I just couldn’t bring myself to tell her.

“If you won’t tell me, I can only presume it involves another man,” she said. “You had a homosexual encounter, that’s nothing to be ashamed of.”

“No. That’s not it,” I tried to assure her. “I promise you, I have never been with a guy.”

She wasn’t convinced and continued to suggest that it was in fact a homosexual experience, otherwise what could I possibly have done that I would be so secretive about. In my drunken state, I caved in to her interrogation and decided to come clean so as to convince her my secret had nothing to do with another man.

“Fine, I will tell you but I trust that it will stay between us, and I hope you don’t think any differently of me,” I said. She nodded in agreement and held her hand to heart as if she were taking an oath of secrecy. “I have had anal sex,” I confessed.

“That’s it?” She was incredulous. “That is the kinkiest thing you’ve ever done? You fucked a girl in the ass? Wow, you are so innocent and boring if you think that’s kinky. That was kinky 100 years ago, but…”

I cut her off mid-sentence. “Uh… I received.” She looked perplexed for a second before realization sunk in. Even though we were alone, I whispered as if there were spies listening in: “Stacy used a strapon on me.” Stacy was my ex-wife.

She clearly hadn’t seen that coming. She sat there in stunned silence for what felt like an eternity, but in reality was probably no more than a few seconds.

Finally, she spoke. “Did you like it? Was it just one time?”

Since it was out in the open, I didn’t see any reason to lie. “Well, the truth is I loved it, and so it was not a one time thing. I’ve experienced it many times.”

“Hmmm…” she said. “I need a drink. Want another?”

That was very abrupt, I thought. I drop that bombshell and she wants to get a drink? I wondered if her opinion of me changed and she now felt uncomfortable knowing what I just told her.

I accepted the drink offer, and as she walked inside to pour a couple of others, I wondered if I said too much. Did she think I was weird, or a pervert? Did she think I was gay? Would she blab my secret to our circle of friends? I sat there with my head in my hands contemplating what just happened.

When she finally came out, I asked if she thought what I had told her was weird.

“No. Not at all. I was just surprised by it, that’s all.”

“Well, then what do you think of that?” I asked. “And please be honest.”

“I… I think it’s great, if you enjoy it,” she stuttered. “I’m all about having fun, and if that rocks your boat, well then, rock on.”

Without my asking, she offered up her kinkiest moment. “I once had a threesome.”

My surprise was mixed with my relief that the discussion was now focused on her. I asked if it was a MMF, MFF or FFF threesome.

Here was her stunner. “Well, neither I suppose. In college, I dated a guy and we hooked up with a shemale. So I don’t know how you’d classify that.”

Wow, I thought my story was interesting! As she explained how they hooked up with uşak escort a shemale, I sat there pondering the logistics of a guy, a girl and a shemale. Maybe it was the alcohol, but I found myself bewildered by the possibilities of who could have done what to whom. So I asked.

“I have always fantasized about shemales. Adam, my boyfriend at the time, was cool with my bringing one in, but refused to do anything with the shemale, even though I think it would’ve been so hot. Anyhow, she called herself ‘Chrissie’ and I had sex with each of them. While one was inside me, I was giving the other a blowjob.”

Jenna volleyed the discussion back at me. “How did you come to experience taking it up the ass?” It was a very forward way of asking, but I have to admit, it turned me on to hear her talk that way.

I gave her as brief an explanation as I possibly could, but made sure to keep in the key details.

“One night Stacy and I were 69’ing,” I told her. “I felt her finger poking around at my butt hole. While it wasn’t an experience I was seeking, I decided not to stop her. I wanted to see where she was going with this, no pun intended. She probably just got past her finger-nail that first time, but still I was overwhelmed by the sensations racing through my body. It was almost too much, too pleasurable. I nearly told her to stop, but just then she started to move her finger back and forth, essentially fucking me with her digit. I couldn’t protest because I couldn’t even speak. All I could do was let out a loud moan. It was — up until that point — the best orgasm I ever experienced.”

Jenna listened intently as I continued. “The fingering became a regular part of our foreplay,” I continued. “Then one day Stacey came home and said she had a present for me. I opened the flowery gift bag she handed me and found a butt plug.

“I was a big fan of her finger, but didn’t know if I was ready to try toys. Later that night, I discovered I was. That eventually led to a small vibrator, then one day to a small dildo.”

“How did it evolve to a strapon?” Jenna asked.

“So one night Stacy is using the dildo on me, with her hand, while I’m on my back. Suddenly, she lifts my legs up and moves close enough so that the dildo is pressed against her pelvis. She started to thrust her hips into me and started talking really dirty.

“Stacey told me, ‘I’m going to buy a strapon so that I can fuck you with it, just like this.’ She kept talking that way and I was enjoying myself so much, that I agreed that I’d love to try it.”

Jenna was fascinated by my experience. Maybe it was the drinks, maybe it was because I also knew of her secret, but I now felt surprisingly comfortable discussing it. I carried on with my story:

“The next day, we bought a harness and that very night, she wore it for the very first time. She didn’t fuck me with it yet, we both wanted to get used to it first. So she wore it while we masturbated together. The next night, we went for it. The rest, as they say, is history.”

This discussion was becoming a little bit too intense for either of us. We decided to end the evening on that note, having exchanged our deepest secrets. I left my car at her place and made the 15 minute walk back to my own, figuring the fresh air would sober me up.

Despite my drunken stupor, I couldn’t help but feel turned on by the fact Jenna now knew about my strapon experience. Of course, the thought of her pegging me crossed my mind and I thought about ways to make it happen. They all seemed pretty far-fetched. By the time I got home, I ripped off all my clothes and had a great jerk-off session, imagining what Jenna would look like wearing nothing but a strapon. I passed out with my cum splattered across my chest.


I awoke late morning to the realization of what I had told Jenna and the paranoia that maybe now that she had time to digest what I said, that maybe she’d be creeped out by it. I was unsure of where things would go from here. Would we ever discuss it again? Or would our secrets hang over us, like the proverbial pink elephant in the room? I decided to go get my car without calling her. Hopefully I could get it, she wouldn’t know until afterwards, and we could delay the eventual awkward first-chat-since.

I was relieved when I arrived that her car was not in the driveway. She was out and so there was no chance of running into her. Later that day, my Blackberry rang and the display read that it was her. I decided not to answer. I waited for the indication of a message, and then listened to it once I saw there was one. Jenna wanted me to come by tonight.

I van escort waited an hour or so before I returned her call. We asked about our mutual hangovers, but aside from that, neither of us brought up last night. She invited me to come over and hang out, as if we hadn’t seen each other in weeks. She rented season 2 of Weeds, a show we had just recently both become fans of. Part of our “divorce therapy” was watching the reruns of season 1. I thought this would be a great idea. Not only did I enjoy the show, but my thinking was we’d be so focused on the episodes, that it would prevent any awkward discussions about last night.

I showed up having picked up some snacks. She asked me to go into the kitchen to pour a couple of glasses of red wine, “the perfect beverage to compliment cheesy nachos,” she joked.

I entered into her living room, drinks in hand. She had already popped in the DVD and sat at her recliner waiting for me. She hit play and we began enjoying the show, pausing the disc occasionally to quickly discuss any particularly interesting or funny scenes.

We got through 5 of the episodes and I suggested we watch the remainder another day. She insisted on one more episode. What’s another half-hour, I decided? I accepted, but told her that was it, one more episode and that would be all. She agreed.

So episode 6 began. It was a great one so far and it came to the funny scene with Andy and the sexy Yael Hoffman enjoying their Jewish dance. The two then took a break where she began to tease and flirt with him, even hinting at getting another woman involved. Well, if you’ve seen this scene, you know where this is going. If you haven’t seen it, then consider this your SPOILER ALERT.

So the scene jumps to the two of them in a bedroom. Andy is giddy on the bed as the gorgeous Meital Dohan (the actress who plays Yael) is wearing sexy lingerie. She reaches under the bed and pulls out a box. My surprised reaction mirrored that of Andy’s as Yael pulled out a strapon harness with a big, black dildo attached. Andy quickly learned that it was for him, and I just as quickly realized Jenna’s suggesting we watch the show, and her insistence on watching this episode, was no coincidence.

I looked over at her, oblivious to the TV and watched as she stood up and removed her kilt, revealing a rubber, and realistic-looking, (Caucasian) skin-coloured strapon hanging from a black harness that hugged her waist and had straps that wrapped around her legs, just under her ass cheeks.

Now here’s where fantasy and reality don’t always mesh. On the surface, this was a fantasy come true. But the reality is that being in this situation with such a close friend felt very, very awkward.

Unfortunately this isn’t as easy as it would seem. This isn’t a corny porno storyline or your typical Literotica fiction. This was real life, and taking this step could pose real ramifications, and what was about to happen could have a great or a disastrous impact on our relationship and perhaps even my privacy.

You see, reading these other stories on this website, the authors usually gloss over the emotional aspect of taking part in sexual activities that are considered by society to be “taboo.” I am your stereotypical guy’s guy. I play hockey with my pals, go for beers afterwards and try to pick up girls any chance I get. The people who know me wouldn’t ever dream that I would be the kind of guy who loves to take it up the ass from a woman wearing a strapon. And a good majority of those people might not think very highly of me if they did know that.

I wasn’t sure how to respond to Jenna’s surprise. All I could do is stare, my mouth agape in shock. She walked over to me bringing the dildo towards my face. “Since your mouth is open anyway…” she said, sliding the toy cock into my open mouth.

In my previous strapon experiences, I never sucked the dildo. It never even occurred to me to do so, and I suppose it never did to Stacy either. But feeling this intrusion into my mouth, looking at how sexy Jenna looked, and the raging hard-on threatening to rip a hole in my jeans, I couldn’t resist giving Jenna what she wanted. I closed my lips around “her cock” and did my best impression of a blowjob.

Though it was an inanimate rubber toy, the psychological aspect of it seemed to bring some level of physical enjoyment to each of us. Jenna moaned in delight as if she really could feel it, and I moaned back loving it as I picked up the pace. I grabbed her ass cheeks to bring her closer to me.

I could rationalize that being pegged with a strapon was a physically enjoyable act, one that few men wouldn’t enjoy, erzincan escort if they allowed themselves to get past the insecurities of doing so. But sucking on this phallic toy shouldn’t bring any sensation to me, but it did. It truly did.

I became a slut for her “cock”, taking it as best as I could, and judging by her reaction and encouragement, I suppose I must have been doing very well.

“That’s it, Stephen, suck it,” she ordered. “That looks so good, you’re a natural cocksucker! Oh, I love it!”

Her praise only made me hornier, and wanting it more and more. I begged her for what I needed: “Please Jenna, fuck my ass with your big cock.”

She let out a laugh, but not a ‘that’s-funny’ laugh, but rather a devious laugh. One that said she was going to give it to me to good, and she couldn’t wait to do so.

I didn’t wait for her to say anything; I just removed my clothes, asking if she had any lube while I did so. Luckily she had obviously been prepared for this and reached under the pillow of her love seat where she hid a tube of K.Y. She turned to find me on my knees, facing the back of her couch, my ass sticking out, waiting for her to mount me.

Jenna stepped in between my feet. “Don’t forget, this is my first time,” she said seriously. “I need you to guide me.”

I knew that was her way of admitting she was afraid of hurting me. I assured her that I’d been ass-fucked enough times that she wouldn’t. Admittedly, I was accustomed to using a plug to loosen myself up, but her dildo was smaller than what I was used to, so I was confident that I could take it without the need of a plug.

Jenna handed me the lube and I turned by body slightly, so that my ass was still sticking out, but I could now see her as she watched me spread lube onto my hand. I then grabbed her dildo and began jerking it off as if it were a real cock that I wanted to keep hard. Again, her moans would have led you to believe she could actually feel the sensation. I then spread the lube on my ass and into my hungry hole.

I reached back again to her cock and brought it towards me, and guided it just enough to poke inside, I then let go and grabbed her hip to push her closer. “Fuck me,” I told her.

With that she thrust forward slowly and with my hand on her hip, I pushed her all the way until she couldn’t go any deeper. I moaned in delight and asked her to hold that position for a few seconds. As my ass familiarized itself with her dildo, she told me how much she was enjoying this new experience.

“This is so fucking hot! You like my cock in your ass, don’t you?”

“Yes,” I told her. I then slid forward, then back again, fucking myself on her dildo. “Make me your bitch,” I begged.

With that, she grabbed hold of my hips and built up a steady rhythm fucking my ass. For a novice, she was a natural ass-fucker.

I stroked my cock as Jenna rammed my ass. It was as enjoyable an ass-fucking as I have ever had. The dildos I usually used were bigger and better than hers, but the fact it was Jenna fucking me more than made up for it. It was the hottest fucking of my life.

I met her thrusts by bouncing on her cock. We would collide with her cock going in as deep as possible. We both worked up a sweat, and I have never felt as submissive as I did at that moment. I was hers, and she knew it.

Jenna slapped my ass, all the while telling me what a slut I was. She leaned forward and moved her hands from hips to my shoulders, using them as leverage to drive her dildo even deeper. I wished at that moment she had a bigger dildo, and I told her that.

“Mmmmm,” she responded between grunts caused by her thrusts. “So you want to be fucked with a BIG cock, do you?” I grunted an affirmative. “That can be arranged,” she continued. “We can definitely get a nice, big hard cock to fuck your ass.”

I couldn’t tell if she was still referring to a fake cock or a real one, but at that point I was feeling too good to make the distinction. Panting hard, I breathlessly admitted, “Yes, Jenna. I want a big, hard cock up my ass.”

This dirty banter had me at the edge. “I’m going to cum,” I shouted. She moved her hand to my cock and I removed mine so that she could finish me off. She continued pounding my ass as her right hand stroked me from behind, the classic reach-around. I let out a loud roar as my cock exploded into her hand. I was like an animal, pulling myself off her cock and turning to kiss her deeply. She instinctively brought her sticky hand to my face, then remembered it was covered in my cum and she instantly pulled it away. I wanted it and grabbed her hand and brought it to my mouth, where I licked her fingers clean, eating my cum. The enjoyment of this act caused my cock to twitch and spurt out more jizz. We kissed some more, and our tongues swished some of my cum in our mouths.

By the time we pulled ourselves apart, we were both out of breath and collapsed onto the floor…

To be continued…

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